Diethyl Ether → 4-Carbobenzoxyoxybenzoic acid 1-methylbutyl ester

HRID 231023Notes

Reaction equation

HRID 231023 reaction equation
[CH2:1]1[CH2:5]OC[CH2:2]1.C(N([CH2:11][CH3:12])CC)C.[C:13]([O:23][C:24]1[CH:32]=[CH:31][C:27]([C:28](Cl)=[O:29])=[CH:26][CH:25]=1)([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14].CC[O:35]CC>>[CH3:2][CH:1]([O:29][C:28](=[O:35])[C:27]1[CH:31]=[CH:32][C:24]([O:23][C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])=[CH:25][CH:26]=1)[CH2:5][CH2:11][CH3:12]

Participants

5

Reactant 4

HCID 3283Diethyl EtherHCID 8028Tetrahydrofuran2×HCID 8471TriethylamineHCID 197340544-Carbobenzoxyoxybenzoyl chloride

Product 1

HCID 542047674-Carbobenzoxyoxybenzoic acid 1-methylbutyl esterYield 13%

Procedure

A THF solution of 0.1 mole of (L)-(-)-2-pentanol and 0.1 mole of triethylamine was stirred at 0° C., and a THF solution of 0.12 mole of 4-carbobenzoxyoxybenzoyl chloride was added dropwise. The temperature was returned to the room temperature slowly, and stirring was carried out for 8 hours. After the reaction, the reaction solution was ether extracted, dried, and concentrated, then purified by column chromatography, to obtain 4.4 g of 4-carbobenzoxyoxybenzoic acid 1-methylbutyl ester. (yield: 13%)

Workup

  1. customwas returned to the room temperature
  2. customAfter the reaction
  3. extractionextracted
  4. customdried
  5. concentrationconcentrated
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-fcb4642c451f470a8a5e885071fdd592
Source dataset
uspto-grants-1989_07
Patent number
US04844835

Reaction notes

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