Hydrochloric Acid → Ethyl 2-hydroxy-6-vinylbenzoate

HRID 2379278Notes

Reaction equation

HRID 2379278 reaction equation
[C:1](=O)([O-])[O-].[Na+].[Na+].[Br-].C([O:11][C:12]1[C:13]([C:38]([O:40][CH2:41][CH3:42])=[O:39])=[C:14]([CH:35]=[CH:36][CH:37]=1)[CH2:15][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(=O)C.C=O.Cl>O>[OH:11][C:12]1[CH:37]=[CH:36][CH:35]=[C:14]([CH:15]=[CH2:1])[C:13]=1[C:38]([O:40][CH2:41][CH3:42])=[O:39]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 10340Sodium CarbonateHCID 10929793(3-Acetyloxy-2-ethoxycarbonylbenzyl)-triphenylphosphonium bromide

Product 1

HCID 15008897Ethyl 2-hydroxy-6-vinylbenzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

A solution of 12.7 g of sodium carbonate in 115 ml of water was added dropwise, while stirring vigorously at room temperate, to 33.8 g of (3-acetoxy-2-ethoxycarbonylbenzyl)triphenylphosphonium bromide (e.g. Eicher et al. Synthesis (1988) 525) in 264 ml of 36.5% by weight aqueous formaldehyde solution. The reaction mixture was stirred at 55° C. for 6 h and then poured into ice-water at pH 1 (hydrochloric acid) and extracted with ethyl acetate, after which the combined organic phases were dried over sodium sulfate and concentrated under reduced pressure. Further purification was carried out by chromatography on silica gel with toluene/ethyl acetate (20:1) as eluent.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialafter which the combined organic phases were dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customFurther purification

Sources & evidence

ORD record
ord-7b88820d46184a56b721433b0d797ec1
Source dataset
uspto-grants-1994_11
Patent number
US05360913

Reaction notes

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