3-Phenoxybenzyl alcohol → 2,2-Dimethyl-3-(3-cyclopropylmethoxy-3-oxo-1-propenyl) cyclopropane-carboxylic acid

HRID 1762622

Reaction equation

HRID 1762622 reaction equation
O(C1C=C(C=CC=1)CO)C1C=CC=CC=1.[CH3:16][C:17]1([CH3:32])[CH:19]([CH:20]=[CH:21][C:22]([O:24][CH2:25][CH:26]2[CH2:28][CH2:27]2)=[O:23])[CH:18]1[C:29]([OH:31])=[O:30]>C(Cl)(Cl)Cl>[CH3:16][C:17]1([CH3:32])[CH:19]([CH:20]=[CH:21][C:22]([O:24][CH2:25][CH:26]2[CH2:28][CH2:27]2)=[O:23])[CH:18]1[C:29]([OH:31])=[O:30].[CH3:16][C:17]1([CH3:32])[CH:19]([CH:20]=[CH:21][C:22]([O:24][CH2:25][CH:26]2[CH2:28][CH2:27]2)=[O:23])[CH:18]1[C:29]([O-:31])=[O:30]

Participants

5

Reactant 2

HCID 262953-Phenoxybenzyl alcoholHCID 539155962,2-Dimethyl-3-(3-cyclopropylmethoxy-3-oxo-1-propenyl) cyclopropane-carboxylic acid

Product 2

HCID 539155962,2-Dimethyl-3-(3-cyclopropylmethoxy-3-oxo-1-propenyl) cyclopropane-carboxylic acidHCID 736755732,2-Dimethyl-3-(3-cyclopropylmethoxy-3-oxo-1-propenyl)-cyclopropane-carboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Using the procedure of Example 9, m-phenoxy-benzyl alcohol and (1R, cis, ΔZ) 2,2-dimethyl-3-(3-cyclopropylmethoxy-3-oxo-1-propenyl)-cyclopropane-carboxylic acid were reacted to obtain m-phenoxy-benzyl (1R, cis, ΔZ) 2,2-dimethyl-3-(3-cyclopropylmethoxy-3-oxo-1-propenyl)-cyclopropane-carboxylate with a specific rotation of [α]D20 =+46.5°±2° (c=0.6% in chloroform).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-f080ea205f164ce587c47687d5a85cb4
Source dataset
uspto-grants-1989_05
Patent number
US04833163

Linked notes

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