Hydroxyphenylacetic acid → HCID 69981182, compound

HRID 1276964Notes

Reaction equation

HRID 1276964 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.CN1CCOCC1.C(OC(Cl)=O)C(C)C.O1CCCC1.[CH2:32]([NH:34][CH2:35][CH2:36][CH3:37])[CH3:33].Cl>O1CCCC1.C(OCC)(=O)C>[CH2:35]([N:34]([CH2:32][CH3:33])[C:9](=[O:11])[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=1)[CH2:36][CH3:37]

Participants

8

Reactant 5

HCID 127Hydroxyphenylacetic acidHCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 883981-Propanamine, N-ethyl-HCID 86756156HCID 86756156, compound

Product 1

HCID 69981182HCID 69981182, compoundYield 93.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-50 °C

Procedure

To a solution of 4-hydroxyphenyl acetic acid (88.43 g, 653 mmol) in 700 mL tetrahydrofuran at -50° C. was added a solution of 4-methylmorpholine (66.1 g, 653 mmol) in 30 mL tetrahydrofuran iso-Butylchloroformate (89.3 g, 653 mmol) was added to the mixture and the resulting solution was stirred at -50° C. for 2 hours. A solution of ethylpropylamine (57 g, 654 mmol) in 30 mL of tetrahydrofuran was added over 15 minutes. After 3 hours, the reaction mixture was poured into a 1:1 mixture of ethyl acetate and 1N hydrochloric acid. The ethyl acetate layer was washed with sodium bicarbonate and brine, then dried over sodium sulfate, filtered and concentrated to give a clear colorless oil (135 g). Purification of the technical grade material was accomplished by crystallization from ethyl acetate.

Workup

  1. additionwas added to the mixture
  2. waitAfter 3 hours
  3. washThe ethyl acetate layer was washed with sodium bicarbonate and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f37a694be9a94fc3bb35d08762e068ba
Source dataset
uspto-grants-2000_12
Patent number
US06166216

Reaction notes

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